Just another approach - I bought a refurbished laptop specifically for my side business for $600 and kept my old personal one separate. Way easier for taxes and mentally helps me separate work mode from personal time. Worth considering if you can swing it financially!

Great question! I'm dealing with something similar as a freelance graphic designer with a regular day job. One thing I'd add to the excellent advice already given - consider the "business use test" timing. The IRS looks at your intent when you purchase the equipment. If you're buying it primarily for your 1099 business (even if you'll use it personally too), that strengthens your deduction position. Also, don't forget about the accessories! If you're getting a monitor, keyboard, mouse, software, etc. for your business setup, those can all be deducted using the same business-use percentage method. I track mine in a simple spreadsheet with purchase date, cost, and estimated business percentage. One tip from my CPA: take photos of your workspace setup and save them with your tax documents. It helps demonstrate the business purpose if you ever need to justify the deduction. Good luck with the new gig and side hustle!

I'm going through the same thing right now! What tax software are you using? I'm on H&R Block and was confused because when I entered my 1099-K, it automatically wanted to treat it as business income on Schedule C which seems wrong for personal items.

I went through this exact same situation last year and completely understand your stress! The key thing to remember is that the 1099-K is just a reporting document - it doesn't automatically mean you owe taxes on the full amount. For personal items sold at a loss (which sounds like your situation), you'll want to report these on Form 8949 and Schedule D, not as business income. The IRS Publication 544 specifically covers sales of personal property and explains that you can use reasonable estimates for cost basis when you don't have original receipts. Here's what worked for me: I created categories for my items (electronics, clothing, books, household items, etc.) and researched what similar items would have cost when I originally bought them. I documented my methodology and kept screenshots of comparable retail prices as backup. For example, if I sold a kitchen appliance from 2015, I looked up what that model cost new in 2015 and used that as my cost basis. The most important thing is to be honest and consistent in your approach. Since you sold personal belongings rather than running a business, you're not trying to claim business deductions - you're just documenting that these sales resulted in losses, not gains. Keep good records of your estimation process and you should be fine!

PSA for everyone: This is exactly why I always pay electronically through the IRS Direct Pay system or EFTPS. No waiting for checks to clear, no wondering if your payment got lost, and you get immediate confirmation. Plus it's free. I learned my lesson years ago after a similar situation.

I'm in almost the exact same boat! Sent my $2,100 check 6 weeks ago and it still hasn't cleared. Reading through these responses is actually making me feel a lot better - sounds like this is pretty normal right now with all the processing delays. I think I'm going to wait another week or two before taking any action, but it's good to know there are options like calling (with help from services like Claimyr if needed) or using those tracking tools people mentioned. For next year I'm definitely switching to electronic payments though - this stress isn't worth it! Thanks everyone for sharing your experiences. It's reassuring to know I'm not the only one dealing with this.

This might sound ridiculous but check if your name has any special characters or if it's extremely long. My husband has a hyphenated last name and we had similar transmission issues until we realized TurboTax was formatting it differently than what the Social Security Administration had on file. Such a stupid problem but took us forever to figure out!

I went through this same nightmare with TurboTax last year! After multiple failed transmission attempts, I discovered the issue was with my bank routing number on the direct deposit section. Even though I had entered it correctly, there was some formatting issue that TurboTax wasn't catching during their review process. Try going to the "Refund" or "Payment" section and double-check ALL your banking information, even if you're sure it's right. Sometimes removing the direct deposit option entirely and choosing to receive a paper check can get past transmission errors. You can always update your banking info with the IRS later if needed. Also, make sure you're filing during off-peak hours - I had much better luck transmitting early in the morning (like 6-7 AM) when their servers aren't overwhelmed. Don't give up! These transmission errors are usually something small and fixable once you identify the actual problem.

Has anyone actually calculated what percentage of their MLP distribution is actually taxable? I have a few energy partnerships and it seems like only about 20-30% of what I receive is currently taxable income. The rest reduces my basis.

I've been through this exact situation with my Energy Transfer LP investment! You're absolutely right to be concerned, but it's not as scary as it seems. The key thing is to be proactive about fixing it. First, gather all your K-1s from the past few years. Energy Transfer usually makes them available online through their investor portal if you've lost the paper copies. The good news is that MLPs like Energy Transfer often have significant depreciation and depletion deductions that can actually reduce your overall tax liability - so you might not owe as much as you think. I'd strongly recommend filing amended returns (Form 1040X) for any years you missed reporting the K-1. Since you're voluntarily correcting this, the IRS tends to be more lenient with penalties. Make sure to include a letter explaining that this was an oversight and that you're proactively correcting it. One tip: if the math gets overwhelming, consider working with a tax professional who has experience with partnership taxation. MLPs can be tricky with all the depreciation recapture rules and basis adjustments, especially if you ever decide to sell. The most important thing is don't wait any longer - file those amended returns as soon as you can get the information together!